Cyclooctylamine → 7-(2-Hydroxy-3-cyclooctylaminopropoxy)-isoflavone hydrochloride

HRID 615881Notes

Reaction equation

HRID 615881 reaction equation
[O:1]1[CH2:22][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:21])[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][O:12]2)=[CH:7][CH:6]=1.[CH:23]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[ClH:32].CCO>CC(O)C>[ClH:32].[OH:1][CH:2]([CH2:22][NH:31][CH:23]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:21])[C:10]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][O:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 2903CyclooctylamineHCID 101084827-(2,3-Epoxypropoxy)-3-phenylchromoneHCID 21887872Ethanol hydrochloride

Product 1

HCID 204068307-(2-Hydroxy-3-cyclooctylaminopropoxy)-isoflavone hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Using Method B, the reaction of 7-(2,3-epoxypropoxy)isoflavone with cyclooctylamine followed by acidification of the resulted free base with HCl/EtOH gave the hydrochloride as light yellow prisms, m.p. 185°-186° (iPrOH).

Sources & evidence

ORD record
ord-774675ad157e41fdb4a0d7016dfe625b
Source dataset
uspto-grants-1985_02
Patent number
US04501755

Reaction notes

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